EP1106169A2 - Emulsionen - Google Patents
Emulsionen Download PDFInfo
- Publication number
- EP1106169A2 EP1106169A2 EP00125866A EP00125866A EP1106169A2 EP 1106169 A2 EP1106169 A2 EP 1106169A2 EP 00125866 A EP00125866 A EP 00125866A EP 00125866 A EP00125866 A EP 00125866A EP 1106169 A2 EP1106169 A2 EP 1106169A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- mol
- oligoesters
- alcohols
- acid
- esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 21
- 229920002601 oligoester Polymers 0.000 claims abstract description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 19
- -1 aromatic dicarboxylic acids Chemical class 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 14
- 239000002202 Polyethylene glycol Substances 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 claims description 2
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 claims description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 2
- 229940045996 isethionic acid Drugs 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 11
- 239000006071 cream Substances 0.000 description 10
- 230000009021 linear effect Effects 0.000 description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 9
- 239000003755 preservative agent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000002335 preservative effect Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 5
- 239000007957 coemulsifier Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 125000003827 glycol group Chemical group 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000037072 sun protection Effects 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 230000000035 biogenic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229940119170 jojoba wax Drugs 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229920000223 polyglycerol Polymers 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- 229940114069 12-hydroxystearate Drugs 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- LAWHHRXCBUNWFI-UHFFFAOYSA-N 2-pentylpropanedioic acid Chemical compound CCCCCC(C(O)=O)C(O)=O LAWHHRXCBUNWFI-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000000973 cosmetic coloring agent Substances 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 1
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- GXJPKIGCMGAHTL-UHFFFAOYSA-N dipropyl benzene-1,4-dicarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)C=C1 GXJPKIGCMGAHTL-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- SFFVATKALSIZGN-UHFFFAOYSA-N hexadecan-7-ol Chemical compound CCCCCCCCCC(O)CCCCCC SFFVATKALSIZGN-UHFFFAOYSA-N 0.000 description 1
- XYXCXCJKZRDVPU-UHFFFAOYSA-N hexane-1,2,3-triol Chemical compound CCCC(O)C(O)CO XYXCXCJKZRDVPU-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960001173 oxybenzone Drugs 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003996 polyglycerol polyricinoleate Substances 0.000 description 1
- 235000010958 polyglycerol polyricinoleate Nutrition 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
Definitions
- oligoesters as so-called soil release polymers (Soil Release Polymers) are used in detergents and cleaning agents. With these Oligoesters are condensation products from dimethyl terephthalate, Ethylene glycol, propylene glycol and polyalkylene glycols. As a result of a molar Excess of the alcohol component contain these oligoester terminal OH groups, which can be completely or partially terminated by alkoxy groups (end caps). Compounds of this type are available under the names ®Milease T, ®Permalose, ®Repel-O-Tex commercially available.
- the invention thus relates to emulsions containing an oligoester.
- oligoesters are preferably obtained by polycondensation of one or more aromatic dicarboxylic acids or their esters and one or more polyhydric alcohols such as ethylene glycol and / or propylene glycol.
- these esters can also include polyethylene glycol, polypropylene glycol, sulfoisophthalic acid, sulfobenzoic acid, isethionic acid, C 1 -C 4 alcohols, oxalkylated C 1 -C 24 alcohols, oxalkylated C 6 -C 18 alkylphenols and / or oxalkylated C 8 -C 24 - Contain alkylamines as monomers.
- Aromatic dicarboxylic acids such as, for example, terephthalic acid, phthalic acid, isophthalic acid and the mono- and dialkyl esters with C 1 - to C 6 -alcohols, such as dimethyl terephthalate, diethyl terephthalate and di-n-propyl terephthalate, are suitable as component a) for the preparation of the oligoesters.
- compositions which can be used as component a) for the preparation of the polyesters are oxalic acid, succinic acid, glutaric acid, adipic acid, fumaric acid, maleic acid, itaconic acid, and the mono- and dialkyl esters of carboxylic acids with C 1 -C 6 alcohols, for example, diethyl oxalate, diethyl succinate, diethyl glutarate, methyl adipate, diethyl adipate, di-n-butyl adipate, ethyl fumarate and dimethyl maleate.
- the anhydrides of the carboxylic acids having at least 2 carboxyl groups are also suitable as a compound of component a) for the preparation of the oligoesters, for example maleic anhydride, phthalic anhydride or succinic anhydride.
- Terephthalic acid, phthalic acid, isophthalic acid and their dimethyl, diethyl, dipropyl and dibutyl esters are particularly preferably used as compounds of component a). It is of course possible to use mixtures of different carboxylic acids or different esters. It is also possible, for example, to use mixtures of carboxylic acids and esters or mixtures of carboxylic acids and anhydrides in the condensation.
- polyethylene glycols with molecular weights from 500 to 5000, preferably from 1000 to 3000.
- Component d) for the preparation of the oligoesters are water-soluble adducts of 5 to 80 mol of at least one alkylene oxide with 1 mol of C 1 -C 24 alcohols, C 6 -C 18 alkylphenols or C 8 -C 24 alkylamines. Monomethyl ethers of polyethylene glycols are preferred.
- the alkylene oxides used to prepare the compounds of component d) are preferably ethylene oxide and mixtures of ethylene oxide and propylene oxide. Mixtures of ethylene oxide together with propylene oxide and / or butylene oxide, mixtures of ethylene oxide, propylene oxide and isobutylene oxide or mixtures of ethylene oxide and at least one butylene oxide are also suitable.
- These water-soluble addition products of the alkylene oxides are surfactants. If mixtures of alkylene oxides are used for their preparation, they can contain the alkylene oxides in blocks or in a statistical distribution.
- Suitable alcohols that are alkoxylated are, for example, octyl alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol or stearyl alcohol, but especially methanol, and the alcohols with 8 to 24 carbon atoms obtainable by the Ziegler process or the corresponding oxo alcohols.
- octylphenol, nonylphenol and dodecylphenol are particularly important.
- polyols examples include pentaerythritol, trimethylolethane, Trimethylolpropane, 1,2,3-hexanetriol, sorbitol, mannitol and glycerin in question.
- the synthesis of the oligoesters according to the invention is carried out according to known methods Process by adding components a, b and c and optionally d a catalyst initially at normal pressure at temperatures from 160 to approx. Be heated to 220 ° C. Then the reaction in vacuo at temperatures of 160 to about 240 ° C continued with distilling off excess glycols.
- a catalyst initially at normal pressure at temperatures from 160 to approx. Be heated to 220 ° C. Then the reaction in vacuo at temperatures of 160 to about 240 ° C continued with distilling off excess glycols.
- the known transesterification and condensation catalysts are suitable for the reaction the prior art, such as titanium tetraisopropylate, dibutyltin oxide or antimony trioxide / calcium acetate.
- EP 442 101 For more details on Implementation of the method is referred to EP 442 101.
- polyesters known from EP 241 985 which contain, in addition to oxyethylene groups and terephthalic acid units, 1,2-propylene, 1,2-butylene and / or 3-methoxy-1,2-propylene groups and glycerol units and with C 1 - to C 4 -alkyl groups are end group-capped;
- Oligoesters of ethylene terephthalate and are also preferred Polyethylene oxide terephthalate in which the polyethylene glycol units have molecular weights have from 750 to 5000 g / mol and the molar ratio of ethylene terephthalate to Polyethylene oxide terephthalate is 50:50 to 90:10 and their use in Detergents is described in German Patent DE 28 57 292, and Oligoesters with molecular weights of 15,000 to 50,000 g / mol from ethylene terephthalate and polyethylene oxide terephthalate, the polyethylene glycol units being molecular weights have from 1000 to 10,000 g / mol and the molar ratio of ethylene terephthalate to polyethylene oxide terephthalate is 2: 1 to 6: 1, which according to DE 33 24 258 in Detergents can be used.
- the oligoesters described are in the emulsions according to the invention usually in amounts of 0.1 to 5, preferably 0.3 to 3 percent by weight, based on the finished emulsion.
- the emulsions can both Water-in-oil emulsions as well as oil-in-water emulsions.
- the non-aqueous part of the emulsions which largely derives from the emulsifier and the oil body and usually the solids content is usually 5 to 95% and preferably 15 to 75% by weight.
- the emulsions 5 to 95 and preferably 25 to 85 wt .-% May contain water, depending on whether or not lotions with a comparative low or creams and ointments with high viscosity are to be produced.
- Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C 6 -C 13 fatty acids with linear C 6 -C 20 fatty alcohols, esters of branched C 6 -C 13 carboxylic acids with linear C 6 -C 20 fatty alcohols, esters of linear C 6 -C 18 fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols (such as dimer diol or trimer diol) and / or Guerbet alcohols, triglycerides based on C 6 -C 10 fatty acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates, dialkyl ethers and / or aliphatic or aromatic hydrocarbons.
- the emulsions can be used as skin care products, such as day creams, Night creams, skin care creams, nutritional creams, body lotions, ointments and the like are used and as further auxiliaries and additives, co-emulsifiers, Superfatting agents, fats, waxes, stabilizers, biogenic agents, glycerin, Contain preservatives, colors and fragrances.
- skin care products such as day creams, Night creams, skin care creams, nutritional creams, body lotions, ointments and the like are used and as further auxiliaries and additives, co-emulsifiers, Superfatting agents, fats, waxes, stabilizers, biogenic agents, glycerin, Contain preservatives, colors and fragrances.
- oligoesters described also without The use of a non-ionic surfactant can be used as a co-emulsifier can.
- the use of co-emulsifiers is therefore not mandatory, however possible.
- Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 C atoms, with fatty acids with 12 to 22 C atoms and with alkylphenols are suitable as nonionogenic O / W co-emulsifiers with 8 to 15 carbon atoms in the alkyl group; C 12 -C 18 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol; Glycerol monoesters and diesters and sorbitan monoesters and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their
- Ethylene oxide addition products Addition products of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil; Polyol and especially polyglycerol esters such as polyglycerol polyricinoleate and polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable.
- the adducts of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products.
- Substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
- Typical examples of fats are glycerides; beeswax, paraffin wax or microwaxes, among others, are suitable as waxes, optionally in combination with hydrophilic waxes, for example cetylstearyl alcohol.
- Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
- Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes.
- Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
- Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
- the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes" by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106.
- the total proportion of auxiliaries and additives can be 1 to 10, preferably 2 to 5% by weight, based on the composition.
- the preparation of the agents can be carried out in a manner known per se, i.e. for example by hot, hot-hot / cold or PIT emulsification.
- Polyester 1 40 mol% terephthalic acid, 10 mol% ethylene glycol, 10 mol% propylene glycol, 20 mol% polyethylene glycol, 10 mol% fatty alcohol ethoxylate, 10 mol% polyol
- Polyester 2 50 mol% terephthalic acid, 25 mol% ethylene glycol, 20 mol% polyethylene glycol, 5 mol% fatty alcohol ethoxylate
- Polyester 3 50 mol% hexanedicarboxylic acid, 40 mol% propylene glycol, 10 mol% polyethylene glycol
- polyesters were produced in the manner described at the outset. The following stability tests were carried out with the formulations described below: Storage at 40 ° C, 45 ° C and 50 ° C for 90 days. Centrifuge at 20 ° C, 5000 rpm, 30 min
- Neo-Heliopan E 1000 Isoamyl p-methoxycinnamate Neo-Heliopan BB Benzophenone-3
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Detergent Compositions (AREA)
Abstract
Description
- R1 und R7
- lineares oder verzweigtes C1- bis C18-Alkyl,
- R2 und R6
- Ethylen,
- R3
- 1,4-Phenylen,
- R4
- Ethylen,
- R5
- Ethylen, 1,2-Propylen oder statistische Gemische von beliebiger Zusammensetzung von beiden,
- x und y
- unabhängig voneinander eine Zahl zwischen 1 und 500,
- z
- eine Zahl zwischen 10 und 140,
- a
- eine Zahl zwischen 1 und 12,
- b
- eine Zahl zwischen 7 und 40,
- R1 und R7
- lineares oder verzweigtes C1- bis C4-Alkyl,
- x und y
- eine Zahl zwischen 3 und 45,
- z
- eine Zahl zwischen 18 und 70,
- a
- eine Zahl zwischen 2 und 5,
- b
- eine Zahl zwischen 8 und 12 und
Der Gesamtanteil der Hilfs- und Zusatzstoffe kann 1 bis 10, vorzugsweise 2 bis 5 Gew.-% bezogen auf das Mittel, betragen.
Polyester 1 | 40 mol% Terephthalsäure, 10 mol% Ethylenglykol, 10 mol% Propylenglykol, 20 mol% Polyethylenglykol, 10 mol% Fettalkoholethoxylat, 10 mol% Polyol |
Polyester 2 | 50 mol% Terephthalsäure, 25 mol% Ethylenglykol, 20 mol% Polyethylenglykol, 5 mol% Fettalkoholethoxylat |
Polyester 3 | 50 mol% Hexandicarbonsäure, 40 mol% Propylenglycol, 10 mol% Polyethylenglykol |
Lagerung bei 40°C, 45°C und 50°C über einen Zeitraum von 90 Tagen. Zentrifugieren bei 20°C, 5000 U/min, 30 min
O/W Creme | |||
A | POLYESTER 1 | (Clariant) | 1,00% |
®Cetiol V | 7,00% | ||
Jojoba oil | 5,00% | ||
Isopropylpalmitat | 6,00% | ||
B | ®Aristoflex AVC | (Clariant) | 0,70% |
C | Glycerin | 3,00% | |
Wasser | 76,90% | ||
Konservierungsmittel | q. s. | ||
D | Parfüm | 0,40% |
Herstellung | |
I | B wurde in A eingerührt, dann wurde C zugegeben und gut gerührt |
II | Unter Rühren wurde D zugegeben |
III | Die Emulsion wurde homogenisiert. |
O/W Creme | |||
A | POLYESTER 2 | (Clariant) | 1,00% |
®Cetiol V | 7,00% | ||
Jojoba oil | 5,00% | ||
Isopropylpalmitat | 6,00% | ||
B | ®Aristoflex AVC | (Clariant) | 0,70% |
C | Glycerin | 3,00% | |
Wasser | 76,90% | ||
Konservierungsmittel | q. s. | ||
D | Parfüm | 0,40% |
O/W Creme | |||
A | POLYESTER 1 | (Clariant) | 1,50% |
Mineralöl, niederviskos | 8,00% | ||
Isopropylpalmitat | 4,00% | ||
®Eutanol G | 4,00% | ||
B | ®Aristoflex AVC | (Clariant) | 0,70% |
C | Wasser | 81,40% | |
Konservierungsmittel | q. s. | ||
D | Parfüm | 0,40% |
O/W Creme | |||
A | POLYESTER 2 | (Clariant) | 1,00% |
Mineralöl, niederviskos | 8,00% | ||
Isopropylpalmitat | 4,00% | ||
®Eutanol G | 4,00% | ||
B | ®Aristoflex AVC | (Clariant) | 0,70% |
C | Wasser | 81,90% | |
Konservierungsmittel | q. s. | ||
D | Parfüm | 0,40% |
O/W Sonnenschutzmilch | |||
A | POLYESTER 1 | (Clariant) | 1,00% |
Mineralöl, hoch viskos | 10,00% | ||
Isopropylpalmitat | 5,00% | ||
B | ®Neo - Heliopan E 1000 | 8,50% | |
®Neo - Heliopan BB | 1,50% | ||
C | Aristoflex AVC | (Clariant) | 0,60% |
D | Glycerin | 3,00% | |
Wasser | 70,10% | ||
Konservierungsmittel | q. s. | ||
E | Parfüm | 0,30% |
Herstellung: | |
I | B wurde mit A gemischt, dann wurde C zugegeben |
II | D wurde unter Rühren zur Mischung I gegeben, dann wurde E zugegeben, |
III | Die Emulsion wurde homogenisiert |
O/W Sonnenschutzmilch | |||
A | POLYESTER 2 | (Clariant) | 1,00% |
Mineralöl, hoch viskos | 10,00% | ||
Isopropylpalmitat | 5,00% | ||
B | ®Neo - Heliopan E 1000 | 8,50% | |
®Neo - Heliopan BB | 1,50% | ||
C | Aristoflex AVC | (Clariant) | 0,60% |
D | Glycerin | 3,00% | |
Wasser | 70,10% | ||
Konservierungsmittel | q. s. | ||
E | Parfüm | 0,30% |
O/W Sonnenschutzmilch | |||
A | POLYESTER 3 | (Clariant) | 2,00% |
Mineralöl, hoch viskos | 10,00% | ||
Isopropylpalmitat | 5,00% | ||
B | ®Neo - Heliopan E 1000 | 8,50% | |
®Neo - Heliopan BB | 1,50% | ||
C | Aristoflex AVC | (Clariant) | 0,60% |
D | Glycerin | 3,00% | |
Wasser | 69,10% | ||
Konservierungsmittel | q. s. | ||
E | Parfüm | 0,30% |
Chemische Bezeichnung der eingesetzten Handelsprodukte: | |
Aristoflex AVC | Acrylamidopropylensulfonsäure/Vinylformamid-Copolymer |
Cetiol | Decyloleat |
Eutanol G | Hexyldecanol |
Neo-Heliopan E 1000 | Isoamyl-p-methoxycinnamate |
Neo-Heliopan BB | Benzophenone-3 |
Claims (5)
- Emulsionen enthaltend Oligoester.
- Emulsionen nach Anspruch 1, dadurch gekennzeichnet, dass sie Oligoester enthalten, die durch Polykondensation von einer oder mehreren Dicarbonsäuren oder deren Ester und einem oder mehreren mehrwertigen Alkoholen erhalten werden.
- Emulsionen nach Anspruch 1, dadurch gekennzeichnet, dass sie Oligoester enthalten, die durch Polykondensation von einer oder mehreren Dicarbonsäuren oder deren Ester und Ethylenglykol und/oder Propylenglykol, sowie gegebenenfalls Polypropylenglykol, Polyethylenglykol, Sulfoisophthalsäure, Sulfobenzoesäure, Isethionsäure, C1-C4-Alkoholen, oxalkylierten C1-C24-Alkoholen, oxalkylierten C6-C18-Alkylphenolen oder oxalkylierten C8-C24-Alkylaminen erhalten werden.
- Emulsionen nach Anspruch 1, dadurch gekennzeichnet, dass sie Oligoester enthalten, die durch Polykondensation vona) 40 bis 52, vorzugsweise 45 bis 50 mol%, einer oder mehrerer aromatischer Dicarbonsäuren oder deren Ester,b) 10 bis 60, vorzugsweise 20 bis 35 mol%, Ethylenglykol und/oder Propylenglykol,c) 0 bis 20, vorzugsweise 10 bis 15 mol%, Polyethylenglykol,d) 0 bis 10 mol% eines wasserlöslichen Anlagerungsproduktes von 5 bis 80 mol eines Alkylenoxids an 1 mol C1-C24-Alkohole, C6-C18-Alkylphenole oder C8-C24-Alkylamine unde) 0 bis 10 mol% eines oder mehrerer Polyole mit 3 bis 6 Hydroxylgruppen erhalten werden.
- Emulsion nach Anspruch 1, dadurch gekennzeichnet, dass sie 0,1 bis 5 Gew.-% Oligoester enthalten.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19959119 | 1999-12-08 | ||
DE19959119A DE19959119A1 (de) | 1999-12-08 | 1999-12-08 | Emulsionen |
Publications (3)
Publication Number | Publication Date |
---|---|
EP1106169A2 true EP1106169A2 (de) | 2001-06-13 |
EP1106169A3 EP1106169A3 (de) | 2001-10-17 |
EP1106169B1 EP1106169B1 (de) | 2005-06-01 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP00125866A Expired - Lifetime EP1106169B1 (de) | 1999-12-08 | 2000-11-25 | Emulsionen |
Country Status (4)
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US (2) | US6489395B2 (de) |
EP (1) | EP1106169B1 (de) |
JP (1) | JP2001226568A (de) |
DE (2) | DE19959119A1 (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1216686A2 (de) * | 2000-12-23 | 2002-06-26 | Beiersdorf Aktiengesellschaft | Gelcrèmes in Form von O/W-Emulsionen mit einem Gehalt an einem oder mehreren Ammoniumacryloyldimethyltaurat/Vinylpyrrolidoncopolymeren |
EP1216695A2 (de) * | 2000-12-23 | 2002-06-26 | Beiersdorf AG | O/W-Emulsionen mit einem Gehalt an Ammoniumacryloyldimethyltaurat/Vinylpyrrolidoncopolymer |
WO2002051377A1 (de) * | 2000-12-23 | 2002-07-04 | Beiersdorf Ag | W/o-emulsionen mit einem gehalt an einem oder mehreren ammoniumacryloyldimethyltaurat/vinylpyrrolidoncopolymeren |
WO2021233987A1 (en) * | 2020-05-20 | 2021-11-25 | Clariant International Ltd | Soil release polyesters for use in detergent compositions |
US11884775B2 (en) | 2017-11-28 | 2024-01-30 | Clariant International Ltd. | Renewably sourced soil release polyesters |
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DE10003137A1 (de) * | 2000-01-26 | 2001-08-02 | Clariant Gmbh | Wäßrige oder wäßrig-alkoholische Körperreinigungsmittel enthaltend Oligoester |
DE10059833A1 (de) * | 2000-12-01 | 2002-06-13 | Clariant Gmbh | Fluormodifizierte Kammpolymere auf Basis von Acryloyldimethylaurinsäure |
DE10065044A1 (de) * | 2000-12-23 | 2002-07-04 | Beiersdorf Ag | Lidschatten auf Gelbasis mit einem Gehalt an einem oder mehreren Ammoniumacryloyldiamethyltaurat/Vinylpyrrolidoncopolymeren |
DE102004029310A1 (de) * | 2004-06-17 | 2005-12-29 | Clariant Gmbh | Hochkonzentrierte, wässrige Formulierungen von Oligo-und Polyestern |
US20060135383A1 (en) * | 2004-12-17 | 2006-06-22 | Cossa Anthony J | Cleansing compositions comprising polymeric emulsifiers and methods of using same |
US20060240144A1 (en) * | 2005-04-21 | 2006-10-26 | Shalaby Shalaby W | Biodegradable chewing gum bases |
US20070092457A1 (en) * | 2005-10-24 | 2007-04-26 | Librizzi Joseph J | Compositions comprising polymeric emulsifiers and methods of using the same |
US20070092458A1 (en) * | 2005-10-24 | 2007-04-26 | Librizzi Joseph J | Compositions comprising polymeric emulsifiers and methods of using the same |
US8425727B2 (en) * | 2010-01-22 | 2013-04-23 | Clariant Finance (Bvi) Limited | Method for increasing glueability of paper or paperboard |
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EP0673638A2 (de) * | 1994-03-24 | 1995-09-27 | Kao Corporation | Antikörper enthaltende kosmetische Zusammensetzung |
FR2760643A1 (fr) * | 1997-03-14 | 1998-09-18 | Rhodia Chimie Sa | Procede de gelification de milieux aqueux, utilisation de copolyesters comme agents gelifiants de milieux aqueux et nouveaux copolyesters gelifiants de milieux aqueux |
FR2781233A1 (fr) * | 1998-07-15 | 2000-01-21 | Rhodia Chimie Sa | Composition polyester terephtalique et son utilisation comme agent antisalissure |
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-
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- 2000-11-25 EP EP00125866A patent/EP1106169B1/de not_active Expired - Lifetime
- 2000-12-07 JP JP2000372726A patent/JP2001226568A/ja not_active Withdrawn
- 2000-12-08 US US09/733,201 patent/US6489395B2/en not_active Ceased
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2004
- 2004-07-16 US US10/893,704 patent/USRE39993E1/en not_active Expired - Fee Related
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EP0673638A2 (de) * | 1994-03-24 | 1995-09-27 | Kao Corporation | Antikörper enthaltende kosmetische Zusammensetzung |
FR2760643A1 (fr) * | 1997-03-14 | 1998-09-18 | Rhodia Chimie Sa | Procede de gelification de milieux aqueux, utilisation de copolyesters comme agents gelifiants de milieux aqueux et nouveaux copolyesters gelifiants de milieux aqueux |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1216686A2 (de) * | 2000-12-23 | 2002-06-26 | Beiersdorf Aktiengesellschaft | Gelcrèmes in Form von O/W-Emulsionen mit einem Gehalt an einem oder mehreren Ammoniumacryloyldimethyltaurat/Vinylpyrrolidoncopolymeren |
EP1216695A2 (de) * | 2000-12-23 | 2002-06-26 | Beiersdorf AG | O/W-Emulsionen mit einem Gehalt an Ammoniumacryloyldimethyltaurat/Vinylpyrrolidoncopolymer |
EP1216695A3 (de) * | 2000-12-23 | 2002-07-03 | Beiersdorf AG | O/W-Emulsionen mit einem Gehalt an Ammoniumacryloyldimethyltaurat/Vinylpyrrolidoncopolymer |
WO2002051377A1 (de) * | 2000-12-23 | 2002-07-04 | Beiersdorf Ag | W/o-emulsionen mit einem gehalt an einem oder mehreren ammoniumacryloyldimethyltaurat/vinylpyrrolidoncopolymeren |
EP1216686A3 (de) * | 2000-12-23 | 2002-07-17 | Beiersdorf Aktiengesellschaft | Gelcrèmes in Form von O/W-Emulsionen mit einem Gehalt an einem oder mehreren Ammoniumacryloyldimethyltaurat/Vinylpyrrolidoncopolymeren |
US11884775B2 (en) | 2017-11-28 | 2024-01-30 | Clariant International Ltd. | Renewably sourced soil release polyesters |
WO2021233987A1 (en) * | 2020-05-20 | 2021-11-25 | Clariant International Ltd | Soil release polyesters for use in detergent compositions |
CN115551984A (zh) * | 2020-05-20 | 2022-12-30 | 科莱恩国际有限公司 | 用于洗涤剂组合物中的去污聚酯 |
Also Published As
Publication number | Publication date |
---|---|
DE50010446D1 (de) | 2005-07-07 |
DE19959119A1 (de) | 2001-06-13 |
EP1106169A3 (de) | 2001-10-17 |
US20010005737A1 (en) | 2001-06-28 |
US6489395B2 (en) | 2002-12-03 |
USRE39993E1 (en) | 2008-01-01 |
JP2001226568A (ja) | 2001-08-21 |
EP1106169B1 (de) | 2005-06-01 |
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